US4033946A - Tetrakisazo dyestuffs - Google Patents
Tetrakisazo dyestuffs Download PDFInfo
- Publication number
- US4033946A US4033946A US05/280,146 US28014672A US4033946A US 4033946 A US4033946 A US 4033946A US 28014672 A US28014672 A US 28014672A US 4033946 A US4033946 A US 4033946A
- Authority
- US
- United States
- Prior art keywords
- sulphonic acid
- dyestuffs
- diaminobenzene
- methyl
- acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
- D06P3/02—Material containing basic nitrogen
- D06P3/04—Material containing basic nitrogen containing amide groups
- D06P3/32—Material containing basic nitrogen containing amide groups leather skins
- D06P3/3206—Material containing basic nitrogen containing amide groups leather skins using acid dyes
- D06P3/3226—Material containing basic nitrogen containing amide groups leather skins using acid dyes dis-polyazo
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
- C09B35/50—Tetrazo dyes
- C09B35/56—Tetrazo dyes of the type
Definitions
- R 1 h or SO 3 H
- Z 1 , z 2 an optionally substituted amino group
- n 1 or 2
- n+ m being ⁇ 3 and wherein the rings A and B may have further substituents, for example, alkoxy groups such as methoxy groups.
- substituents R there may be mentioned in particular: optionally substituted alkyl groups, in particular such with 1-4 C atoms, halogen, in particular chlorine.
- n-substituents R can be the same or different. This likewise applies to the substituents R 1 and Z 1 -Z 2 .
- substituents Z 1 -Z 2 there may be mentioned in particular amino groups as well as aminoalkylamino groups such as C 1 -C 4 alkyl groups, optionally substituted by hydroxyl, sulphonic acid or caboxylic acid groups.
- R' h, ch 3 , cl.
- n 1 or 2
- n 1 or 2
- n+ m being ⁇ 3.
- Suitable coupling components (V) are 2-amino-8-hydroxynaphthalene-6-sulphonic acid and 2-amino-8-hydroxynaphthalene-3,6-disulphonic acid or mixtures of both.
- Suitable coupling components (VII) are for example: 1,3-diaminobenzene-4-sulphonic acid, 1-methyl-2,6-diaminobenzene-4-sulphonic acid, 1-chloro-2,6,-diaminobenzene-4-sulphonic acid, 1-amino-3-hydroxy-ethylamino-benzene-6-sulphonic acid, 1-methyl-2-hydroxyethylaminobenzene-4-sulphonic acid, 1-methyl-2-carboxy-methylamino-6-aminobenzene-4-sulphonic acid, 1-methyl-2-sulpho-methylamino-6-aminobenzene-4-sulphonic acid, 1-chloro-2-carboxy-methylamino-6-aminobenzene-sulphonic acid, 1-chloro-2-sulphomethyl-amino-6-aminobenzene-4-sulphonic acid, 1-chloro-2-hydroxymethylamino-6-aminobenzene-4-s
- the new dyestuffs are suitable for the dyeing and printing of natural fibre materials, especially leather. Black dyeings are obtained on leather with good fastness properties.
- 28 g of 4,4'-diamino-diphenylamine-2'-sulphonic acid are tetrazotised in a known manner and coupled in an alkaline medium onto 48 g of 2-amino-8-hydroxy-6-sulphonic acid.
- the resulting diamino-disazo dyestuff is further tetrazotised and coupled in an alkaline medium with 39 g of 1,3-diaminobenzene-4-sulphonic acid.
- the dyestuff precipitated by the addition of sodium chloride and then isolated is easily soluble in water and dyes leather black. The dyeings possess good fastness properties.
- 28 g of 4,4'-diamino-diphenylamine-2'-sulphonic acid are tetrazotised in a known manner and coupled in an alkaline medium onto 64 g of 2-amino-8-hydroxynaphthalene-3,6-disulphonic acid.
- the resulting diaminodisazo dyestuff is further tetrazotised and coupled onto 39 g of 1,3-diaminobenzene-4-sulphonic acid.
- the dyestuff precipitated by the addition of sodium chloride and then isolated is easily soluble in water and dyes leather black.
- Unsymmetrically synthesised dyestuffs which are likewise suitable for dyeing leather, are obtained, if during the end coupling stage half of the amount each of for example 1-chloro-2,6-diaminobenzene-4-sulphonic acid and 1,3-diaminobenzene-4-sulphonic acid or another suitable component is used.
- the end components (total of 2 mol) required for the end coupling can also of course be used in any other molar ratio.
- 28 g of 4,4'-diamino-diphenylamine-2-sulphonic acid are tetrazotised in a known manner and coupled in an alkaline medium one after the other or simultaneously with 24 g of 2-amino-8-hydroxynaphthalene-6-sulphonic acid and 32 g of 2-amino-8-hydroxynaphthalene-3,6-disulphonic acid.
- the resulting unsymmetrical diamino-disazo dyestuff is further tetrazotised and coupled in an alkaline medium with 42 g of 1-methyl-2,4-diamino-benzene-5-sulphonic acid. After precipitation by the addition of sodium chloride and isolation the black dye is easily soluble in water and particularly suitable for dyeing leather.
- black dyestuffs are also produced having good solubility and particularly good suitability for dyeing leather.
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DT2140867 | 1971-08-14 | ||
DE2140867A DE2140867C3 (de) | 1971-08-14 | 1971-08-14 | Tetrakisazofarbstoffe, deren Herstellung und Verwendung |
Publications (1)
Publication Number | Publication Date |
---|---|
US4033946A true US4033946A (en) | 1977-07-05 |
Family
ID=5816795
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US05/280,146 Expired - Lifetime US4033946A (en) | 1971-08-14 | 1972-08-14 | Tetrakisazo dyestuffs |
Country Status (11)
Country | Link |
---|---|
US (1) | US4033946A (xx) |
JP (1) | JPS4828035A (xx) |
BE (1) | BE787481A (xx) |
CH (1) | CH574480A5 (xx) |
DD (1) | DD100486A5 (xx) |
DE (1) | DE2140867C3 (xx) |
ES (1) | ES405806A1 (xx) |
FR (1) | FR2149418B1 (xx) |
GB (1) | GB1348217A (xx) |
IT (1) | IT968368B (xx) |
NL (1) | NL7211085A (xx) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4242258A (en) * | 1978-02-21 | 1980-12-30 | Hoechst Aktiengesellschaft | Water-soluble dyestuffs, processes for their manufacture, their use as fiber-reactive dyestuffs for dyeing and printing fiber materials and the fiber materials dyed with these dyestuffs |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3520389A1 (de) * | 1985-06-07 | 1986-12-11 | Bayer Ag, 5090 Leverkusen | Tetrakis-azofarbstoffe |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US1078926A (en) * | 1913-04-01 | 1913-11-18 | Farbenfab Vorm Bayer F & Co | Blue azo dyes. |
US2096896A (en) * | 1936-02-05 | 1937-10-26 | Gen Aniline Works Inc | Azodyestuffs |
FR966768A (fr) * | 1941-07-24 | 1950-10-18 | Cie Nat Matieres Colorantes | Colorants polyazoïques et leur procédé de préparation |
GB1019467A (en) * | 1962-12-22 | 1966-02-09 | Cassella Farbwerke Mainkur Ag | New tetrakisazo dyestuffs and process for their production |
GB1105350A (en) * | 1965-12-11 | 1968-03-06 | Cassella Farbwerke Mainkur Ag | Tetrakisazo dyestuffs |
-
1971
- 1971-08-14 DE DE2140867A patent/DE2140867C3/de not_active Expired
-
1972
- 1972-08-11 BE BE787481D patent/BE787481A/xx unknown
- 1972-08-11 JP JP47080036A patent/JPS4828035A/ja active Pending
- 1972-08-11 FR FR7229019A patent/FR2149418B1/fr not_active Expired
- 1972-08-11 CH CH1194772A patent/CH574480A5/xx not_active IP Right Cessation
- 1972-08-11 DD DD165015A patent/DD100486A5/xx unknown
- 1972-08-12 ES ES405806A patent/ES405806A1/es not_active Expired
- 1972-08-12 IT IT28197/72A patent/IT968368B/it active
- 1972-08-14 NL NL7211085A patent/NL7211085A/xx not_active Application Discontinuation
- 1972-08-14 US US05/280,146 patent/US4033946A/en not_active Expired - Lifetime
- 1972-08-14 GB GB3782772A patent/GB1348217A/en not_active Expired
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US1078926A (en) * | 1913-04-01 | 1913-11-18 | Farbenfab Vorm Bayer F & Co | Blue azo dyes. |
US2096896A (en) * | 1936-02-05 | 1937-10-26 | Gen Aniline Works Inc | Azodyestuffs |
FR966768A (fr) * | 1941-07-24 | 1950-10-18 | Cie Nat Matieres Colorantes | Colorants polyazoïques et leur procédé de préparation |
GB1019467A (en) * | 1962-12-22 | 1966-02-09 | Cassella Farbwerke Mainkur Ag | New tetrakisazo dyestuffs and process for their production |
GB1105350A (en) * | 1965-12-11 | 1968-03-06 | Cassella Farbwerke Mainkur Ag | Tetrakisazo dyestuffs |
Non-Patent Citations (1)
Title |
---|
Colour Index, 2 ed. (1957), vol. 3, p. 3306, CI. 35445, CI. 35435 & CI. 35450. * |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4242258A (en) * | 1978-02-21 | 1980-12-30 | Hoechst Aktiengesellschaft | Water-soluble dyestuffs, processes for their manufacture, their use as fiber-reactive dyestuffs for dyeing and printing fiber materials and the fiber materials dyed with these dyestuffs |
Also Published As
Publication number | Publication date |
---|---|
GB1348217A (en) | 1974-03-13 |
CH574480A5 (xx) | 1976-04-15 |
FR2149418B1 (xx) | 1976-08-13 |
DE2140867C3 (de) | 1976-01-08 |
ES405806A1 (es) | 1975-07-16 |
NL7211085A (xx) | 1973-02-16 |
DE2140867B2 (xx) | 1975-04-30 |
JPS4828035A (xx) | 1973-04-13 |
IT968368B (it) | 1974-03-20 |
BE787481A (fr) | 1973-02-12 |
DE2140867A1 (de) | 1973-02-15 |
DD100486A5 (xx) | 1973-09-20 |
FR2149418A1 (xx) | 1973-03-30 |
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